Nineteen polychlorinated biphenyl (PCB) congeners, such as 2,2′,3,3′,6-pentachlorobiphenyl (PCB 84), display axial chirality because they form stable rotational isomers, or atropisomers, that are non-superimposable mirror images of each other. Although chiral PCBs undergo atropselective biotransformation and atropselectively alter biological processes, the absolute structure of only a few PCB atropisomers has been determined experimentally. To help close this knowledge gap, pure PCB 84 atropisomers were obtained by semi-preparative liquid chromatography with two serially connected Nucleodex β-PM columns. The absolute configuration of both atropisomers was determined by X-ray single-crystal diffraction. The PCB 84 atropisomer eluting first and second on the Nucleodex β-PM column correspond to (aR)-(−)-PCB 84 and (aS)-(+)-PCB 84, respectively. Enantioselective gas chromatographic analysis with the β-cyclodextrin-based CP-Chirasil-Dex CB gas chromatography column showed the same elution order as the Nucleodex β-PM column. Based on earlier reports, the atropisomers eluting first and second on the BGB-172 gas chromatography column are (aR)-(−)-PCB 84 and (aS)-(+)-PCB 84, respectively. An inversion of the elution order is observed on the Cyclosil-B gas chromatography and Cellulose-3 liquid chromatography columns. These results advance the interpretation of environmental and human biomonitoring as well as toxicological studies.

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Published in Environmental Science and Pollution Research, v. 25, issue 17, p. 16402-16410.

© Springer-Verlag Berlin Heidelberg 2017

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This is a post-peer-review, pre-copyedit version of an article published in Environmental Science and Pollution Research. The final authenticated version is available online at: https://doi.org/10.1007/s11356-017-9259-z.

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This work was supported by grants ES05605, ES013661 and ES017425 from the National Institute of Environmental Health Sciences/National Institutes of Health. The X8 Proteum diffractometer was funded by the National Science Foundation (MRI CHE0319176), and by the University of Kentucky (cost share).

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